Citation: Long-Fei Yuan, Yu-Jian He, Hong Zhao, Ying Zhou, Pei Gu. Colorimetric detection of D-amino acids based on anti-aggregation of gold nanoparticles[J]. Chinese Chemical Letters, ;2014, 25(7): 995-1000. doi: 10.1016/j.cclet.2014.06.002 shu

Colorimetric detection of D-amino acids based on anti-aggregation of gold nanoparticles

Long-Fei Yuan ^a ,
Yu-Jian He ^a,b,, ,
Hong Zhao ^a ,
Ying Zhou ^a ,
Pei Gu ^a,,

1.
a College of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China;
2.
b State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

Corresponding author: Yu-Jian He, Pei Gu,
Received Date: 1 April 2014
Available Online: 28 May 2014
Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21272263) (No. 21272263) the University of Chinese Academy of Sciences (No. 08JT011J01) (No. K20130206)the Twelfth Five-Year Plan for National Sciences &Technology Support Project (No. 2012BAI37B03) (No. 08JT011J01)

A new method has been proposed to realize the visual detection of D-amino acids (DAAs) via the antiaggregation of 4-mercaptobenzoic acid modified gold nanoparticles (AuNPs) in the presence of D-amino acid oxidase (DAAO). The negatively charged AuNPs were prepared using sodium citrate as a reducer and stabilizer. The presence of 4-mercaptobenzoic acid (4-MBA) and Cu²⁺ induces the aggregation of AuNPs, resulting in a color change from ruby red to royal purple. However, DAAO could oxidize DAAs to generate H₂O₂. In the presence of H₂O₂, the mercapto (-SH) group in 4-mercaptobenzoic acid can be oxidized to form a disulfide (-S-S-) bond. Based on these facts, the pre-incubation of DAAs and 4-mercaptobenzoic acid with DAAO would significantly reduce the concentration of free 4-mercaptobenzoic acidmolecules, thus the aggregation of AuNPs was interrupted since due to the lack of inducer. As the concentration of DAAs increases, the color of the AuNPs solution would progress from royal purple to ruby red. Consequently, DAAs could be monitored by the colorimetric response of AuNPs using a UV-vis spectrophotometer or even naked eyes. This DAAO mediated visual detectionmethod could determine Dalanine (D-Ala) as a representative DAA with concentrations ranging from 1.5×10^-7 mol L^-1 to 3.0×10^-5 mol L^-1, and the detection limit was as low as 7.5×10^-8 mol L^-1. The proposed method is convenient, low-cost and free of complex equipment, making it feasible to analyze the concentration of D-Ala in real samples of β-amyloid peptide (Aβ_1-42).
- Gold nanoparticles,
- D-Amino acids,
- D-Amino acid oxidase,
- Anti-aggreagtion,
- Colorimetric detection
1. [1]
  [1] M. Friedman, Chemistry, nutrition, and microbiology of D-amine acids, J. Agric. Food Chem. 47 (1999) 3457-3479.
2. [2]
  [2] C. Henneberger, T. Papouin, S.H.R. Oliet, et al., Long-term potentiation depends on release of D-serine from astrocytes, Nature 463 (2010) 232-236.
3. [3]
  [3] I. Azua, I. Goiriena, Z. Bana, et al., Release and consumption of D-amino acids during growth of marine prokaryotes, Microb. Ecol. 67 (2014) 1-12.
4. [4]
  [4] V. Vranova, H. Zahradnickova, D. Janous, et al., The significance of D-amino acids in soil, fate and utilization by microbes and plants: review and identification of knowledge gaps, Plant Soil 354 (2012) 21-39.
5. [5]
  [5] S.A. Fuchs, R. Berger, L.W.J. Klomp, et al., D-amino acids in the central nervous system in health and disease, Mol. Genet. Metab. 85 (2005) 168-180.
6. [6]
  [6] H. Wolosker, E. Dumin, L. Balan, V.N. Foltyn, D-amino acids in the brain: D-serine in neurotransmission and neurodegeneration, FEBS J. 275 (2008) 3514-3526.
7. [7]
  [7] G.H. Fisher, L. Petrucelli, C. Gardner, et al., Free D-amino acids in human cerebrospinalfluid of Alzheimer-disease, multiple-sclerosis, and healthy control subjects, Mol. Chem. Neuropathol. 23 (1994) 115-124.
8. [8]
  [8] S. Kato, Y. Kito, H. Hemmi, T. Yoshimura, Simultaneous determination of D-amino acids by the coupling method of D-amino acid oxidase with high-performance liquid chromatography, J. Chromatogr. B 879 (2011) 3190-3195.
9. [9]
  [9] C. Mueller, J.R. Fonseca, T.M. Rock, S. Krauss-Etschmann, P. Schmitt-Kopplin, Enantioseparation and selective detection of D-amino acids by ultra-high-performance liquid chromatography/mass spectrometry in analysis of complex biological samples, J. Chromatogr. A 1324 (2014) 109-114.
10. [10]
  [10] Y. Gogami, K. Okada, T. Oikawa, High-performance liquid chromatography analysis of naturally occurring D-amino acids in sake, J. Chromatogr. B 879 (2011) 3259-3267.
11. [11]
  [11] H. Brückner, A. Schieber, Determination of free D-amino acids in mammalia by chiral gas chromatography-mass spectrometry, J. High Resolut. Chromatogr. 23 (2000) 576-582.
12. [12]
  [12] R. Patzold, H. Bruckner, Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell, Amino Acids 31 (2006) 63-72.
13. [13]
  [13] R. Patzold, A. Schieber, H. Bruckner, Gas-chromatographic quantification of free Damino acids in higher vertebrates, Biomed. Chromatogr. 19 (2005) 466-473.
14. [14]
  [14] C.H. Nieh, Y. Kitazumi, O. Shirai, K. Kano, Sensitive D-amino acid biosensor based on oxidase/peroxidase system mediated by pentacyanoferrate-bound polymer, Biosens. Bioelectron. 47 (2013) 350-355.
15. [15]
  [15] S. Lata, B. Batra, C.S. Pundir, Construction of D-amino acid biosensor based on Damino acid oxidase immobilized onto poly (indole-5-carboxylic acid)/zinc sulfide nanoparticles hybrid film, Process Biochem. 47 (2012) 2131-2138.
16. [16]
  [16] S. Lata, B. Batra, P. Kumar, et al., Construction of an amperometric D-amino acid biosensor based on D-amino acid oxidase/carboxylated mutliwalled carbon nanotube/ copper nanoparticles/polyalinine modified gold electrode, Anal. Biochem. 437 (2013) 1-9.
17. [17]
  [17] E. Rosini, G. Molla, C. Rossetti, et al., A biosensor for all D-amino acids using evolved D-amino acid oxidase, J. Biotechnol. 135 (2008) 377-384.
18. [18]
  [18] Y.C. Cao, R.C. Jin, S. Thaxton, et al., A two-color-change, nanoparticle-based method for DNA detection, Talanta 67 (2005) 449-455.
19. [19]
  [19] H. Chi, B.H. Liu, G.J. Guan, et al., A simple, reliable and sensitive colorimetric visualization of melamine in milk by unmodified gold nanoparticles, Analyst 135 (2010) 1070-1075.
20. [20]
  [20] F. Li, Y. Feng, C. Zhao, et al., Simple colorimetric sensing of trace bleomycin using unmodified gold nanoparticles, Biosens. Bioelectron. 26 (2011) 4628-4631.
21. [21]
  [21] C.D. Medley, J.E. Smith, Z. Tang, et al., Gold nanoparticle-based colorimetric assay for the direct detection of cancerous cells, Anal. Chem. 80 (2008) 1067-1072.
22. [22]
  [22] H. Li, Y.W. Yang, Gold nanoparticles functionalized with supramolecular macrocycles, Chin. Chem. Lett. 24 (2013) 545-552.
23. [23]
  [23] B.H. Wu, H.Y. Yang, H.Q. Huang, et al., Solvent effect on the synthesis of monodisperse amine-capped Au nanoparticles, Chin. Chem. Lett. 24 (2013) 457-462.
24. [24]
  [24] S. Link, M.A. El-Sayed, Spectral properties and relaxation dynamics of surface plasmon electronic oscillations in gold and silver nanodots and nanorods, J. Phys. Chem. B 103 (1999) 8410-8426.
25. [25]
  [25] Y.P. Li, L. Jiang, T. Zhang, et al., Colorimetric detection of glucose using a boronic acid derivative receptor attached to unmodified AuNPs, Chin. Chem. Lett. 25 (2014) 77-79.
26. [26]
  [26] R. Elghanian, J.J. Storhoff, R.C. Mucic, et al., Selective colorimetric detection of polynucleotides based on the distance-dependent optical properties of gold nanoparticles, Science 277 (1997) 1078-1081.
27. [27]
  [27] C.Y. Lin, C.J. Yu, Y.H. Lin, W.L. Tseng, Colorimetric sensing of silver(I) and mercury(II) ions based on an assembly of Tween 20-stabilized gold nanoparticles, Anal. Chem. 82 (2010) 6830-6837.
28. [28]
  [28] N. Ding, H. Zhao, W.B. Peng, et al., A simple colorimetric sensor based on antiaggregation of gold nanoparticles for Hg²⁺ detection, Colloids Surf. A-Physicochem. Eng. Aspect 395 (2012) 161-167.
29. [29]
  [29] J.S. Lee, M.S. Han, C.A. Mirkin, Colorimetric detection of mercuric ion (Hg²⁺) in aqueous media using DNA-functionalized gold nanoparticles, Angew. Chem. Int. Ed. 46 (2007) 4093-4096.
30. [30]
  [30] Y. Xue, H. Zhao, Z.J. Wu, et al., Colorimetric detection of Cd²⁺ using gold nanoparticles cofunctionalized with 6-mercaptonicotinic acid and L-cysteine, Analyst 136 (2011) 3725-3730.
31. [31]
  [31] Y. Zhou, P.L. Wang, X.O. Su, et al., Colorimetric detection of ractopamine and salbutamol using gold nanoparticles functionalized with melamine as a probe, Talanta 112 (2013) 20-25.
32. [32]
  [32] X.F. Zhang, H. Zhao, Y. Xue, et al., Colorimetric sensing of clenbuterol using gold nanoparticles in the presence of melamine, Biosens. Bioelectron. 34 (2012) 112-117.
33. [33]
  [33] X.F. Zhang, Y. Zhang, H. Zhao, et al., Highly sensitive and selective colorimetric sensing of antibiotics in milk, Anal. Chim. Acta 778 (2013) 63-69.
34. [34]
  [34] X.F. Zhang, Z.J. Wu, Y. Xue, et al., Colorimetric detection of melamine based on the interruption of the synthesis of gold nanoparticles, Anal. Methods 5 (2013) 1930-1934.
35. [35]
  [35] Z.J. Wu, H. Zhao, Y. Xue, et al., Colorimetric detection of melamine during the formation of gold nanoparticles, Biosens. Bioelectron. 26 (2011) 2574-2578.
36. [36]
  [36] Q.A. Cao, H. Zhao, Y.J. He, et al., Hydrogen-bonding-induced colorimetric detection of melamine by nonaggregation-based Au-NPs as a probe, Biosens. Bioelectron. 25 (2010) 2680-2685.
37. [37]
  [37] Y. Zhou, H. Zhao, Y.J. He, N. Ding, Q. Cao, Colorimetric detection of Cu²⁺ using 4-mercaptobenzoic acid modified silver nanoparticles, Colloid Surf. A-Physicochem. Eng. Aspect 391 (2011) 179-183.
38. [38]
  [38] Y.C. Shiang, C.C. Huang, H.T. Chang, Gold nanodot-based luminescent sensor for the detection of hydrogen peroxide and glucose, Chem. Commun. (2009) 3437-3439.
39. [39]
  [39] A.R. Quesada, R.W. Byrnes, S.O. Krezoski, et al., Direct reaction of H₂O₂ with sulfhydryl groups in HL-60 cells: zinc-metallothionein and other sites, Arch. Biochem. Biophys. 334 (1996) 241-250.
40. [40]
  [40] B. Cardey,M. Enescu, Selenocysteine versus cysteine reactivity: a theoretical study of their oxidation by hydrogen peroxide, J. Phys. Chem. A 111 (2007) 673-678.
41. [41]
  [41] J. Wang, D.M. Wang, Y.F. Li, Study of cysteine modified gold nanoparticles as a colorimetric detection platform for oxidants, Chin. Sci. Bull. 56 (2011) 1196-1203.
42. [42]
  [42] L.F. Yuan, Y.J. He, Effect of surface charge of PDDA-protected gold nanoparticles on the specificity and efficiency of DNA polymerase chain reaction, Analyst 138 (2013) 539-545.
43. [43]
  [43] X.H. Ji, X.N. Song, J. Li, et al., Size control of gold nanocrystals in citrate reduction: the third role of citrate, J. Am. Chem. Soc. 129 (2007) 13939-13948.
44. [44]
  [44] A. Daniello, A. Vetere, G.H. Fisher, et al., Presence of D-alanine in proteins of normal and Alzheimer human brain, Brain Res. 592 (1992) 44-48.
45. [45]
  [45] K. Wiesehan, K. Buder, R.P. Linke, et al., Selection of D-amino-acid peptides that bind to Alzheimer's disease amyloid peptide Aβ_1-42 by mirror image phage display, Chembiochem 4 (2003) 748-753.
46. [46]
  [46] Y.S. Shim, W.J. Yoon, J. Ha, et al., Method validation of 16 types of structural amino acids using an automated amino acid analyzer, Food Sci. Biotechnol. 22 (2013) 1567-1571.
47. [47]
  [47] S.V. Khoronenkova, V.I. Tishkov, D-amino acid oxidase: physiological role and applications, Biochemistry (Mosc.) 73 (2008) 1511-1518.
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